diff --git a/app/builders/messages/message_builder.rb b/app/builders/messages/message_builder.rb
index af312bf2e..0ec73edc3 100644
--- a/app/builders/messages/message_builder.rb
+++ b/app/builders/messages/message_builder.rb
@@ -9,11 +9,11 @@ class Messages::MessageBuilder
     @user = user
     @message_type = params[:message_type] || 'outgoing'
     @attachments = params[:attachments]
-    @automation_rule = @params&.dig(:content_attributes, :automation_rule_id)
+    @automation_rule = content_attributes&.dig(:automation_rule_id)
     return unless params.instance_of?(ActionController::Parameters)
 
-    @in_reply_to = params.to_unsafe_h&.dig(:content_attributes, :in_reply_to)
-    @items = params.to_unsafe_h&.dig(:content_attributes, :items)
+    @in_reply_to = content_attributes&.dig(:in_reply_to)
+    @items = content_attributes&.dig(:items)
   end
 
   def perform
@@ -26,6 +26,38 @@ class Messages::MessageBuilder
 
   private
 
+  # Extracts content attributes from the given params.
+  # - Converts ActionController::Parameters to a regular hash if needed.
+  # - Attempts to parse a JSON string if content is a string.
+  # - Returns an empty hash if content is not present, if there's a parsing error, or if it's an unexpected type.
+  def content_attributes
+    params = convert_to_hash(@params)
+    content_attributes = params.fetch(:content_attributes, {})
+
+    return parse_json(content_attributes) if content_attributes.is_a?(String)
+    return content_attributes if content_attributes.is_a?(Hash)
+
+    {}
+  end
+
+  # Converts the given object to a hash.
+  # If it's an instance of ActionController::Parameters, converts it to an unsafe hash.
+  # Otherwise, returns the object as-is.
+  def convert_to_hash(obj)
+    return obj.to_unsafe_h if obj.instance_of?(ActionController::Parameters)
+
+    obj
+  end
+
+  # Attempts to parse a string as JSON.
+  # If successful, returns the parsed hash with symbolized names.
+  # If unsuccessful, returns nil.
+  def parse_json(content)
+    JSON.parse(content, symbolize_names: true)
+  rescue JSON::ParserError
+    {}
+  end
+
   def process_attachments
     return if @attachments.blank?
 
diff --git a/app/javascript/dashboard/api/inbox/message.js b/app/javascript/dashboard/api/inbox/message.js
index fc77b24f5..6cb885e3d 100644
--- a/app/javascript/dashboard/api/inbox/message.js
+++ b/app/javascript/dashboard/api/inbox/message.js
@@ -26,9 +26,13 @@ export const buildCreatePayload = ({
     payload.append('echo_id', echoId);
     payload.append('cc_emails', ccEmails);
     payload.append('bcc_emails', bccEmails);
+
     if (toEmails) {
       payload.append('to_emails', toEmails);
     }
+    if (contentAttributes) {
+      payload.append('content_attributes', JSON.stringify(contentAttributes));
+    }
   } else {
     payload = {
       content: message,
diff --git a/app/javascript/dashboard/api/specs/inbox/message.spec.js b/app/javascript/dashboard/api/specs/inbox/message.spec.js
index e75bf34b0..0d45b2157 100644
--- a/app/javascript/dashboard/api/specs/inbox/message.spec.js
+++ b/app/javascript/dashboard/api/specs/inbox/message.spec.js
@@ -50,6 +50,7 @@ describe('#ConversationAPI', () => {
         message: 'test content',
         echoId: 12,
         isPrivate: true,
+        contentAttributes: { in_reply_to: 12 },
         files: [new Blob(['test-content'], { type: 'application/pdf' })],
       });
       expect(formPayload).toBeInstanceOf(FormData);
@@ -57,6 +58,10 @@ describe('#ConversationAPI', () => {
       expect(formPayload.get('echo_id')).toEqual('12');
       expect(formPayload.get('private')).toEqual('true');
       expect(formPayload.get('cc_emails')).toEqual('');
+      expect(formPayload.get('bcc_emails')).toEqual('');
+      expect(formPayload.get('content_attributes')).toEqual(
+        '{"in_reply_to":12}'
+      );
     });
 
     it('builds object payload if file is not available', () => {
diff --git a/app/javascript/dashboard/components/widgets/conversation/Message.vue b/app/javascript/dashboard/components/widgets/conversation/Message.vue
index 920d115b5..363003982 100644
--- a/app/javascript/dashboard/components/widgets/conversation/Message.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/Message.vue
@@ -38,6 +38,7 @@
           v-if="inReplyToMessageId && inboxSupportsReplyTo"
           :message="inReplyTo"
           :message-type="data.message_type"
+          :parent-has-attachments="hasAttachments"
         />
         <bubble-text
           v-if="data.content"
diff --git a/app/javascript/dashboard/components/widgets/conversation/bubble/ReplyTo.vue b/app/javascript/dashboard/components/widgets/conversation/bubble/ReplyTo.vue
index fb557293b..7bc4d5156 100644
--- a/app/javascript/dashboard/components/widgets/conversation/bubble/ReplyTo.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/bubble/ReplyTo.vue
@@ -5,7 +5,7 @@
       'bg-slate-100 dark:bg-slate-600 dark:text-slate-50':
         messageType === MESSAGE_TYPE.INCOMING,
       'bg-woot-600 text-woot-50': messageType === MESSAGE_TYPE.OUTGOING,
-      '-mx-2': message.content,
+      '-mx-2': !parentHasAttachments,
     }"
   >
     <message-preview
@@ -34,6 +34,10 @@ export default {
       type: Number,
       required: true,
     },
+    parentHasAttachments: {
+      type: Boolean,
+      required: true,
+    },
   },
   data() {
     return { MESSAGE_TYPE };
diff --git a/app/models/channel/telegram.rb b/app/models/channel/telegram.rb
index ffc6433b2..ac2f4b9be 100644
--- a/app/models/channel/telegram.rb
+++ b/app/models/channel/telegram.rb
@@ -77,8 +77,16 @@ class Channel::Telegram < ApplicationRecord
     errors.add(:bot_token, 'error setting up the webook') unless response.success?
   end
 
+  def chat_id(message)
+    message.conversation[:additional_attributes]['chat_id']
+  end
+
+  def reply_to_message_id(message)
+    message.content_attributes['in_reply_to_external_id']
+  end
+
   def send_message(message)
-    response = message_request(message.conversation[:additional_attributes]['chat_id'], message.content, reply_markup(message))
+    response = message_request(chat_id(message), message.content, reply_markup(message), reply_to_message_id(message))
     response.parsed_response['result']['message_id'] if response.success?
   end
 
@@ -115,24 +123,26 @@ class Channel::Telegram < ApplicationRecord
       telegram_attachments << telegram_attachment
     end
 
-    response = attachments_request(message.conversation[:additional_attributes]['chat_id'], telegram_attachments)
+    response = attachments_request(chat_id(message), telegram_attachments, reply_to_message_id(message))
     response.parsed_response['result'].first['message_id'] if response.success?
   end
 
-  def attachments_request(chat_id, attachments)
+  def attachments_request(chat_id, attachments, reply_to_message_id)
     HTTParty.post("#{telegram_api_url}/sendMediaGroup",
                   body: {
                     chat_id: chat_id,
-                    media: attachments.to_json
+                    media: attachments.to_json,
+                    reply_to_message_id: reply_to_message_id
                   })
   end
 
-  def message_request(chat_id, text, reply_markup = nil)
+  def message_request(chat_id, text, reply_markup = nil, reply_to_message_id = nil)
     HTTParty.post("#{telegram_api_url}/sendMessage",
                   body: {
                     chat_id: chat_id,
                     text: text,
-                    reply_markup: reply_markup
+                    reply_markup: reply_markup,
+                    reply_to_message_id: reply_to_message_id
                   })
   end
 end
diff --git a/app/services/telegram/incoming_message_service.rb b/app/services/telegram/incoming_message_service.rb
index 51a99b4fb..7b0c9faec 100644
--- a/app/services/telegram/incoming_message_service.rb
+++ b/app/services/telegram/incoming_message_service.rb
@@ -19,6 +19,7 @@ class Telegram::IncomingMessageService
       inbox_id: @inbox.id,
       message_type: :incoming,
       sender: @contact,
+      content_attributes: telegram_params_content_attributes,
       source_id: telegram_params_message_id.to_s
     )
 
diff --git a/app/services/telegram/param_helpers.rb b/app/services/telegram/param_helpers.rb
index 5accae1f1..6201fa0f3 100644
--- a/app/services/telegram/param_helpers.rb
+++ b/app/services/telegram/param_helpers.rb
@@ -6,6 +6,13 @@ module Telegram::ParamHelpers
     params.dig(:message, :chat, :type) == 'private'
   end
 
+  def telegram_params_content_attributes
+    reply_to = params.dig(:message, :reply_to_message, :message_id)
+    return { 'in_reply_to_external_id' => reply_to } if reply_to
+
+    {}
+  end
+
   def message_params?
     params[:message].present?
   end
diff --git a/spec/builders/messages/message_builder_spec.rb b/spec/builders/messages/message_builder_spec.rb
index 728cb8cf1..891f8eb02 100644
--- a/spec/builders/messages/message_builder_spec.rb
+++ b/spec/builders/messages/message_builder_spec.rb
@@ -8,6 +8,7 @@ describe Messages::MessageBuilder do
   let(:inbox) { create(:inbox, account: account) }
   let(:inbox_member) { create(:inbox_member, inbox: inbox, account: account) }
   let(:conversation) { create(:conversation, inbox: inbox, account: account) }
+  let(:message_for_reply) { create(:message, conversation: conversation) }
   let(:params) do
     ActionController::Parameters.new({
                                        content: 'test'
@@ -21,6 +22,75 @@ describe Messages::MessageBuilder do
     end
   end
 
+  describe '#content_attributes' do
+    context 'when content_attributes is a JSON string' do
+      let(:params) do
+        ActionController::Parameters.new({
+                                           content: 'test',
+                                           content_attributes: "{\"in_reply_to\":#{message_for_reply.id}}"
+                                         })
+      end
+
+      it 'parses content_attributes from JSON string' do
+        message = described_class.new(user, conversation, params).perform
+        expect(message.content_attributes).to include(in_reply_to: message_for_reply.id)
+      end
+    end
+
+    context 'when content_attributes is a hash' do
+      let(:params) do
+        ActionController::Parameters.new({
+                                           content: 'test',
+                                           content_attributes: { in_reply_to: message_for_reply.id }
+                                         })
+      end
+
+      it 'uses content_attributes as provided' do
+        message = described_class.new(user, conversation, params).perform
+        expect(message.content_attributes).to include(in_reply_to: message_for_reply.id)
+      end
+    end
+
+    context 'when content_attributes is absent' do
+      let(:params) do
+        ActionController::Parameters.new({ content: 'test' })
+      end
+
+      it 'defaults to an empty hash' do
+        message = message_builder
+        expect(message.content_attributes).to eq({})
+      end
+    end
+
+    context 'when content_attributes is nil' do
+      let(:params) do
+        ActionController::Parameters.new({
+                                           content: 'test',
+                                           content_attributes: nil
+                                         })
+      end
+
+      it 'defaults to an empty hash' do
+        message = message_builder
+        expect(message.content_attributes).to eq({})
+      end
+    end
+
+    context 'when content_attributes is an invalid JSON string' do
+      let(:params) do
+        ActionController::Parameters.new({
+                                           content: 'test',
+                                           content_attributes: 'invalid_json'
+                                         })
+      end
+
+      it 'defaults to an empty hash' do
+        message = message_builder
+        expect(message.content_attributes).to eq({})
+      end
+    end
+  end
+
   describe '#perform when message_type is incoming' do
     context 'when channel is not api' do
       let(:params) do
diff --git a/spec/models/channel/telegram_spec.rb b/spec/models/channel/telegram_spec.rb
index 4fe49f844..0fa5515fb 100644
--- a/spec/models/channel/telegram_spec.rb
+++ b/spec/models/channel/telegram_spec.rb
@@ -10,7 +10,7 @@ RSpec.describe Channel::Telegram do
 
       stub_request(:post, "https://api.telegram.org/bot#{telegram_channel.bot_token}/sendMessage")
         .with(
-          body: 'chat_id=123&text=test&reply_markup='
+          body: 'chat_id=123&text=test&reply_markup=&reply_to_message_id='
         )
         .to_return(
           status: 200,
@@ -32,7 +32,7 @@ RSpec.describe Channel::Telegram do
         .with(
           body: 'chat_id=123&text=test' \
                 '&reply_markup=%7B%22one_time_keyboard%22%3Atrue%2C%22inline_keyboard%22%3A%5B%5B%7B%22text%22%3A%22test%22%2C%22' \
-                'callback_data%22%3A%22test%22%7D%5D%5D%7D'
+                'callback_data%22%3A%22test%22%7D%5D%5D%7D&reply_to_message_id='
         )
         .to_return(
           status: 200,